Dimethylformamide → HCID 66971957, compound

HRID 1364194Notes

Reaction equation

HRID 1364194 reaction equation
N1C(=O)CC[C@@H]1C(O)=O.[NH2:10][C@@H:11]1[CH2:17][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[NH:13][C:12]1=[O:22].CN(C)C=O.C(N(CC)CC)C.[C:35](Cl)([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(OCC)C>[C:35]([NH:10][C@@H:11]1[CH2:17][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[NH:13][C:12]1=[O:22])([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 10881289HCID 10881289, compound

Product 1

HCID 66971957HCID 66971957, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

A round-bottom flask was fitted with a condenser, stirbar and septa. 3(R)-Amino-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one D-pyroglutamic acid salt (10.0 g, 32.8 mmol), N,N-dimethylformamide (200 mL) and triethylamine (12 mL, 86.1 mmol) were added, giving a mixture which was heated to 120° C. To the resulting solution was added trityl chloride (9.04 g, 32.4 mmol). The reaction was then cooled to 60° C., maintained at 60° C. for 4 hours, and then allowed to slowly cool to room temperature. After 18 hours, the reaction mixture was diluted with diethyl ether (300 mL) and washed first with 400 mL 1:1 H2O:saturated aqueous NaCl solution, then with 2×100 mL H2O. The aqueous washes were combined and extracted with diethyl ether (100 mL). The organic extracts were combined, dried over MgSO4, filtered and concentrated in vacuo to give an oil which that purified via flash chromatography on silica gel (25% ethyl acetate/hexanes) to give the desired product.

Workup

  1. customA round-bottom flask was fitted with a condenser
  2. customgiving a mixture which
  3. temperatureThe reaction was then cooled to 60° C.
  4. temperaturemaintained at 60° C. for 4 hours
  5. temperatureto slowly cool to room temperature
  6. washwashed first with 400 mL 1:1 H2O
  7. extractionextracted with diethyl ether (100 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto give an oil which that
  12. custompurified via flash chromatography on silica gel (25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b363f8a8c0a84989aac0c9788c00cf7f
Source dataset
uspto-grants-2011_02
Patent number
US07888345B2

Reaction notes

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